WO2009068193A2 - Combinaison herbicide-azole - Google Patents

Combinaison herbicide-azole Download PDF

Info

Publication number
WO2009068193A2
WO2009068193A2 PCT/EP2008/009681 EP2008009681W WO2009068193A2 WO 2009068193 A2 WO2009068193 A2 WO 2009068193A2 EP 2008009681 W EP2008009681 W EP 2008009681W WO 2009068193 A2 WO2009068193 A2 WO 2009068193A2
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
methyl
group
herbicide
substituted
Prior art date
Application number
PCT/EP2008/009681
Other languages
German (de)
English (en)
Other versions
WO2009068193A3 (fr
Inventor
Arne Brink
Rolf Pontzen
Stefan Dutzmann
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to US12/743,738 priority Critical patent/US8318637B2/en
Priority to EP08855397A priority patent/EP2224813A2/fr
Publication of WO2009068193A2 publication Critical patent/WO2009068193A2/fr
Publication of WO2009068193A3 publication Critical patent/WO2009068193A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the invention is in the technical field of pesticides which are useful against harmful plants e.g. can be used in crops and relates to a combination of specific herbicides with agrochemically active azole compounds.
  • compositions which contain a herbicide a) and a Bioeid b), as well as an antidote c), which counteracts by the Bioeid b) increased phytotoxic effect of the herbicide a).
  • the object of the present invention was to provide an improved herbicidally active ingredient combination.
  • herbicides from the group of ALS inhibitors in combination with agrochemical active compounds from the group of azoles interact in a particularly favorable manner and show, for example, synergistic effects.
  • the invention thus provides a herbicide-azole combination with a content of components A) and B), wherein
  • Suitable ALS inhibitors A) are, for example, compounds from the group of imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives or the sulfonamides, such as Triazolopyrimidinesulfonamides, sulfonylaminocarbonyltriazolinones or sulfonylureas.
  • Preferred sulfonamides are, for example, phenylsulfonamides, heteroarylsulfonamides and sulfonediamides (for example cyclosulfamuron or (alkylsulfonyl) alkylamino-sulfonamides, such as amidosulfuron).
  • Suitable phenylsulfonamides A) are compounds from the group of the phenylsulfonylaminocarbonyltriazolinones or the phenylsulfonylureas, preferably from the group of the phenylsulfonylureas.
  • the term phenylsulfonylureas is also understood to mean those sulfonylureas in which the phenyl group is attached to the groups via a spacer such as CH 2 , O or NH
  • Sulfone group (SO 2 ) is bound.
  • phenylsulfonylaminocarbonyl-triazolinones are flucarbazones or propoxycarbazones and / or salts thereof.
  • the ALS inhibitors A) are commercially available and / or can be prepared by known processes as described, for example, in EP-A-7687, EP-A-30138, US Pat. No. 5,057,144 and US Pat. No. 5,534,486.
  • Suitable phenylsulfonamides are, for example, phenylsulfonamides of the general formula (I) and / or salts thereof,
  • R ⁇ is a phenyl radical which is unsubstituted or substituted, and wherein the phenyl radical including substituents has 1 to 30 C atoms, preferably 1 to 20 C atoms, R ⁇ is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and inclusive Substituents 1-10 C atoms, for example unsubstituted or substituted C 1 -C 6 -alkyl, preferably a hydrogen atom or methyl,
  • R ⁇ is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and contains, including substituents, 1-10 C atoms, for example unsubstituted or substituted C 1 -C 6 -alkyl, preferably a hydrogen atom or methyl,
  • A is CH 2 , O or NH, preferably O, m is zero or 1, n is zero or 1, preferably 1, and
  • R ⁇ is a heterocyclic radical such as a pyrimidinyl radical, a triazinyl radical or a triazolinone radical.
  • Preferred phenylsulfonamides are phenylsulfonylureas, for example phenylsulfonylureas of the general formula (II) and / or salts thereof,
  • R ⁇ is a phenyl radical which is unsubstituted or substituted, and wherein the phenyl radical including substituents has 1-30 C atoms, preferably 1-20 C atoms, R p is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and inclusive Substituents 1-10 C atoms, for example unsubstituted or substituted Ci-Ce-alkyl, preferably a hydrogen atom or methyl,
  • R ⁇ is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and contains 1-10 C atoms inclusive of substituents, for example unsubstituted or substituted C 1 -C 6 -alkyl, preferably a hydrogen atom or methyl, A is CH 2 , O or NH, preferably O, m is zero or 1, and R ⁇ is a heterocyclic radical such as a pyrimidinyl radical or a triazinyl radical.
  • R 6 is H or C 1 -C 4 -alkyl, m is zero or 1,
  • X and Y are independently the same or different halogen or NR'R ", wherein R 'and R" or differently, H or CrC are equal to 4 alkyl, or -C 6 - alkyl, C r C 6 alkoxy, -C 6 alkylthio, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -
  • Alkynyl, C 3 -C 6 alkenyloxy or C 3 -C 6 -alkyl are kynyloxy, each of the eight last-mentioned radicals being unsubstituted or substituted by one or more radicals from the group halogen, -C 4 alkoxy and C r C 4 alkylthio is preferably C 1 -C 4 alkyl or C 1 -C 4 alkoxy and Z is CH or N.
  • R 4 is CO- (C 1 -C 4 -alkoxy), R 5 is halogen, preferably iodine, or R 5 is CH 2 -NHR 6 wherein R 6 is an acyl group, preferably -C 4 alkyl-sulfonyl, and m is equal to zero
  • R 4 is CO-N (C r C 4 alkyl) 2
  • R 5 is NHR e wherein R e is an acyl radical, preferably formyl, and m is zero
  • R 4 is C 2 -C 4 alkoxy
  • R 5 is H
  • m is 1.
  • Typical phenylsulfonylureas include the following compounds and their salts, such as the sodium salts: Bensulfuron-methyl, Chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron and its sodium salt, metsulfuron-methyl, oxasulfuron, primisulfuron-methyl, prosulfuron, sulfometuron-methyl, triasulfuron, tribenuronmethyl, triflusulfuron-methyl, tritosulfuron, lodosulfuron- methyl and its sodium salt, mesosulfuron-methyl and its sodium salt and foramsulfuron and its sodium salt.
  • Particularly preferred phenylsulfonamides are: iodosulfuron-methyl (A1.1) and its salts, such as the sodium salt (A1.2), mesosulfuron-methyl (A2.1) and its salts, such as the sodium salt (A2.2), foramsulfuron (A3.1 ) and its salts, such as the sodium salt (A3.2), flucarbazone (A4.1) and its salts, such as the sodium salt (A4.2), propoxycarbazone (A5.1) and its salts, such as the sodium salt (A5.2) and ethoxysulfuron (A6.1) and its salts such as the sodium salt (A6.2), metsulfuron-methyl (A7.1) and its salts such as the sodium salt (A7.2), tribenuron-methyl (A8.1) and its salts such as Sodium salt (A8.2), chlorosulfuron (A9.1) and its salts, such as the sodium salt (A9.2).
  • heteroarylsulfonylaminocarbonyltriazolinones or heteroarylsulfonylureas preferably from the group of
  • Heteroarylsulfonylureas are also understood as meaning those sulfonylureas in which the heteroaryl group is attached via a spacer such as Chfe, O or NH to the
  • Sulfone group (SO 2 ) is bound.
  • heteroarylsulfonamides for example, sulfonamides of the general
  • R ⁇ ' is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and has 1-10 C atoms inclusive of substituents, for example unsubstituted or substituted C 1 -C 6 -alkyl, preferably one
  • a ' is CH 2 , O or NH, preferably O, m is zero or 1, n' is zero or 1, preferably 1, and R ⁇ 'is a heterocyclic radical such as pyrimidinyl, triazinyl or a
  • Triazolinone is.
  • heteroarylsulfonamides are heteroarylsulfonylureas, for example sulfonylureas of the general formula (V) and / or salts thereof,
  • R 0 is a heteroaryl radical which is unsubstituted or substituted, and where the heteroaryl radical including substituents has 1-30 C atoms, preferably 1-20 C atoms,
  • R ⁇ l is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and having 1-10 carbon atoms including substituents, for example unsubstituted or substituted Ci-Ce-alkyl, preferably a hydrogen atom or methyl
  • R ⁇ ⁇ is a hydrogen atom or a hydrocarbon radical which is unsubstituted or substituted and contains 1-10 C atoms inclusive of substituents, for example unsubstituted or substituted C 1 -C 6 -alkyl, preferably one
  • R ⁇ l is a heterocyclic radical such as a pyrimidinyl radical or a triazinyl radical.
  • heteroarylsulfonamides of the following formula (VI),
  • R ⁇ l is a triazolinone radical , preferably
  • R 7 is (Ci -Ci o) alkyl, which is optionally substituted with halogen (F, Cl, Br, I) or
  • (dC 3 ) Halo-alkyl, X and Y independently of one another are identical or different halogen or NR'R ", in which R 'and R" are, identically or differently, H or C 1 -C 4 -alkyl, or C 1 -C 6 -alkyl, C 1 -C 4 -alkyl Alkoxy, C 1 -C 6 -alkylthio, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -alkenyloxy or C 3 -C 6 -alkynyloxy, wherein each of the eight the latter radicals unsubstituted or substituted by one or more radicals from the group halogen, C 1 -GrAIkOXy and dC-rAlkylthio, preferably CrC 4 alkyl or CrC-j-alkoxy.
  • R 0 is the same
  • R 9 (C r C6) alkyl, (C 1 -C 6) -alkoxy, (C 2 -C 6) alkenyloxy, (C 2 -C 6) alkynyloxy, (Ci-C 6) alkylsulfonyl, (Ci-C 6 ) Alkylcarbonyl, (C 1 -C 6 ) alkoxycarbonyl,
  • R 10 is H, (CrC 3) alkyl, (C 1 -C 3) -alkoxy, (C r C 3) halo alkyl, (C 1 -C 3) -alkoxy or Haio
  • Halogen (F, Cl, Br, I), I is zero or 1
  • R 11 (C r C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (C 2 -C 6 ) alkynyloxy, (C 2 -C 6 ) alkynyloxy, (C r C 6 ) alkylsulfonyl, (C r C 6) alkylcarbonyl, (C r C 6) alkoxycarbonyl,
  • R 13 (CrC 6) alkoxycarbonyl, (C 2 -C 6) alkenyloxycarbonyl, (C2 -Ce) alkynyloxycarbonyl, (CrC 6) alkyl, (C 1 -C 6) -alkoxy, (d-CeJAlkylsulfonyl, (C r C 6 ) Halo-alkoxycarbonyl, (C 2 -C 6 ) halo-alkenyloxycarbonyl, (C 2 -C 6 ) halo-alkynyloxycarbonyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) halogenoalkoxy 1 ( CrC 6 ) haloalkylsulfonyl, halogen (F, Cl, Br, I),
  • CONR'R ", or R 13 is a heterocyclic ring which may be saturated, unsaturated or aromatic and preferably contains 4-6 ring atoms and one or more heteroatoms from the group N, O, S, and optionally by one or more substituents, preferably from the group (C 1 - C 3) alkyl, (C 1 -C 3) -alkoxy, (CrC 3) halo alkyl, (C 1 -C 3) -alkoxy or halogen Haio may be substituted, more preferably
  • R 14 H halogen (F, C, Br, I), (C r C 6 ) alkyl, (C r C 6 ) halo-alkyl, R 15 H, (CrC 6 ) alkyl, (C r C 6 ) halo Alkyl, R 16 (C r C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (C 2 -C 6 ) alkenyloxy, (C 2 -C 6 ) alkynyloxy, (C r C 6 ) alkylsulfonyl, (C r C 6) alkylcarbonyl, (C r C6) alkoxycarbonyl, (C 2 -C 6) alkenyloxycarbonyl, (C 2 -C 6) alkynyloxycarbonyl, (CrC 6) alkyl-halo, (C 1 -C 6) -alkoxy Haio , (C 2 -C 6) halo-al
  • R 'and R "independently of one another are H, (C r C 6 ) alkyl, (C r C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) Alkynyl, (C 2 -C 6 ) haloalkynyl, or NR'R "forms a heterocyclic ring which may be saturated, unsaturated or aromatic and preferably 4-6 ring atoms and one or more heteroatoms from the group N, O, S, and optionally by one or more substituents, preferably from the group (CrC 3 ) alkyl, (Ci-Ca) Al koxy, (Ci-C 3 ) halo-alkyl, (C r C 3 ) Halo-alkoxy or halogen may be substituted.
  • heteroarylsulfonylureas are e.g. Nicosulfuron (A10.1) and its salts, such as the sodium salt (A10.2), rimsulfuron (A11.1) and its salts, such as the sodium salt (A11.2), thifensulfuron-methyl (A12.1) and its salts, such as the sodium salt (A12.2), pyrazosulfuron-ethyl (A13.1) and its salts, such as the sodium salt (A13.2), flupyrsulfuron-methyl (A14.1) and its salts, such as the sodium salt (A14.2), sulfosulfuron (A15.
  • Nicosulfuron (A10.1) and its salts such as the sodium salt (A10.2), rimsulfuron (A11.1) and its salts, such as the sodium salt (A11.2), thifensulfuron-methyl (A12.1) and its salts, such as the sodium salt (A12.2), pyrazos
  • heteroarylsulfonylaminocarbonyltriazolinones are thiencarbazone-methyl (A20.1) and its salts, such as the sodium salt (A20.2).
  • Suitable ALS inhibitors are e.g.
  • Imidazolinones e.g.
  • Very particularly preferred ALS inhibitors A) are sulfonamides, e.g. iodosulfuron-methyl (A1.1), iodosulfuron-methyl-sodium (A1.2), mesosulfuron-methyl (A2.1), mesosulfuron-methyl-sodium (A2.2), flucarbazone (A4.1), flucarbazone-sodium (A4.2), propoxycarbazone (A5.1) and propoxycarbazone sodium (A5.2).
  • iodosulfuron-methyl A1.1
  • iodosulfuron-methyl-sodium A1.2
  • mesosulfuron-methyl A2.1
  • mesosulfuron-methyl-sodium A2.2
  • flucarbazone A4.1
  • flucarbazone-sodium A4.2
  • propoxycarbazone A5.1
  • propoxycarbazone sodium A5.2
  • the active ingredients listed above are e.g. known from "The Pesticide Manual", 14th edition (2006), The British Crop Protection Council or the references listed after the individual active ingredients.
  • ALS inhibitors A) used in the combinations according to the invention always includes all forms of use such as acids, esters, salts and isomers, such as stereoisomers and optical isomers.
  • their salts with inorganic and / or organic counterions are always to be understood.
  • sulfonamides can form salts in which the hydrogen of the -SO 2 -NH group is replaced by a cation suitable for agriculture.
  • These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts or salts with organic amines.
  • salt formation can take place by addition of an acid to basic groups, such as, for example, amino and alkylamino.
  • Suitable acids for this purpose are strong inorganic and organic acids, for example HCl, HBr, H 2 SO 4 or HNO 3 .
  • Preferred esters are the alkyl esters, in particular Ci-C-O-alkyl esters as ⁇ Methylester.
  • acyl radical in this description, this means the radical of an organic acid which forms formally by elimination of an OH group from the organic acid, for example the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted Iminocarboxylic acids or the residues of carbonic acid monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
  • the radical of an organic acid which forms formally by elimination of an OH group from the organic acid for example the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted Iminocarboxylic acids or the residues of carbonic acid monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids
  • An acyl radical is preferably formyl or acyl from the group CO-R Z, CS-R Z, CO-OR 2, CS-OR 2, CS-SR Z, SOR 2 or SO 2 R 2, wherein R 2 are each a C r Ci 0 -
  • Hydrocarbon radical such as CrCi O -alkyl or C ⁇ -Cio-aryl which is unsubstituted or substituted, for example by one or more substituents selected from the group halogen such as F, Cl, Br, I, alkoxy, haloalkoxy, hydroxy, amino, nitro, cyano or alkylthio, or R z denotes aminocarbonyl or aminosulfonyl, where the last two radicals mentioned are unsubstituted, N-monosubstituted or N, N-disubstituted, for example by substituents from the group consisting of alkyl or aryl.
  • substituents selected from the group halogen such as F, Cl, Br, I, alkoxy, haloalkoxy, hydroxy, amino, nitro, cyano or alkylthio, or R z denotes aminocarbonyl or aminosulfonyl, where the last two radicals mentioned are unsubstituted,
  • Acyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl, such as (C 1 -C 4 ) -alkylcarbonyl, phenylcarbonyl, where the phenyl ring may be substituted, or alkyloxycarbonyl, such as (C 1 -C 4 ) -alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, such as (C 1 -C 4 ) Alkylsulfonyl, alkylsulfinyl, such as Cr
  • N-alkyl-1-iminoalkyl such as N- (CrC 4 ) -1-imino- (C- ⁇ -C 4 ) alkyl and other radicals of organic acids.
  • a hydrocarbon radical means a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic
  • Hydrocarbon radical e.g. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl.
  • a hydrocarbon radical preferably has 1 to 40 C atoms, preferably 1 to 30 C atoms; particularly preferably a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 C atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring may be saturated, unsaturated or heteroaromatic and unsubstituted or substituted; it preferably contains one or more heteroatoms in the ring, preferably from the group N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3 heteroatoms.
  • the heterocyclic radical may be, for example, a heteroaromatic radical or ring (heteroaryl), for example a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, Thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, triazolyl, dioxolanyl, morpholinyl, tetrahydrofuryl.
  • heteroaryl for example a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms, for example pyridyl, pyr
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below in question, in addition also oxo.
  • the oxo group may also occur on the hetero ring atoms, which may exist in different oxidation states, eg at N and S.
  • Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, represent, for example, a substituted radical derived from the unsubstituted radical, where the substituents are, for example, one or more, preferably 1, 2 or 3 3 radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido,
  • Alkenyloxy, alkynyloxy, etc. mean.
  • substituents from the group halogen, for example fluorine and chlorine (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy or ethoxy, ( Ci-C 4 ) haloalkoxy, nitro and cyano.
  • substituents for example fluorine and chlorine
  • (C 1 -C 4 ) alkyl preferably methyl or ethyl
  • C 1 -C 4 ) haloalkyl preferably trifluoromethyl
  • C 1 -C 4 alkoxy preferably methoxy or ethoxy
  • Ci-C 4 ) haloalkoxy nitro and cyano.
  • substituents methyl, methoxy and chlorine are particularly preferred.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals, preferably from the group halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 -haloalkyl, (dC -OHalogenalkoxy and nitro, for example, o-, m- and p-tolyl, dimethylphenyl, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro and trichlorophenyl, 2,4-, 3 , 5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
  • Cycloalkyl means a carbocyclic saturated ring system preferably having 3-6 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • the carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case be straight-chain or branched. Unless specifically stated, these radicals are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean e.g.
  • AIIyI 1-methyl p-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methyl-but-2-en-1-yl;
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • Halogen is, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkyl, -alkenyl and -alkynyl by halogen preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl;
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • Suitable components B) are agrochemical active substances, preferably fungicidal active compounds, from the group of the triazoles, pyrazoles or triazolinethiones, preferably from the group of the triazoles, e.g. the following active ingredients (in each case the CAS number of at least one preferred form is given in brackets behind the compounds, in particular a commercially available form):
  • B1 azaconazole (60207-31-0), B2: bromuconazole (116255-48-2), B3: cyproconazole (113096-99-4), B4: diclobutrazoles (75736-33-3), B5: difenoconazole (119446- 68-3), B6: diniconazole (83657-24-3), B7: diniconazole-M (83657-18-5), B8: epoxiconazole (106325-08-0), B9: etaconazole (60207-93-4) , B10: fenbuconazole (114369-43-6), B11: fluquinconazole (136426-54-5), B12: flusilazole (85509-19-9), B13: furconazole (112839-33-5), B14: hexaconazole (79983 -71-4), B15: imibenconazole (86598-92-7), B16: ipconazole (125225
  • B21 prothioconazole (178928-70-6), B22: quinconazole (13970-75-8), B23: simeconazole (149508-90-7), B24: tebuconazole (107534-96-3), B25: tetraconazole (112281- 77-3), B26: triticonazole (131983-72-7), B27: uniconazole (83657-22-1), B28: viniconazole (77174-66-4), B29: voriconazole (137234-62-9), B30 : (1- (4-chlorophenyl) -2- (1H-1,2,4-triazoM-yl) cycloheptanol (129586-32-9), B31: triadimenol (55219-65-3; 89482-17-7 82200-72-4), B32: triadimefon (43121-43-3), B33: bitertanol (70585-36-3, 70585-38-5, 55179-31-2
  • Particularly preferred azoles B) are cyproconazole (B3), epoxiconazole (B8), fluquinconazole (B11), propiconazole (B20), prothioconazole (B21), tebuconazole (B24) and myclobutanil (B35).
  • the herbicide-azole combinations according to the invention generally have an effective content of components A) and B) and may additionally contain further components, for.
  • the herbicide-azole combinations according to the invention have a synergistically effective content of components A) and B).
  • the synergistic effects in particular synergistic herbicidal effects, may e.g. when co-application of the active ingredients A) and B) are observed, but they can often also be delayed
  • split application are detected. It is also possible to use the individual active ingredients or the herbicide-azole combinations in several portions (sequence application), z. After pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the joint or timely use of the active ingredients of the herbicide-azole combination according to the invention.
  • the synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency at the same rate, the control of previously unrecognized species (gaps), an extension of the period of application and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and ecologically more beneficial weed control systems.
  • the abovementioned formulas (I) - (VI) include all stereoisomers and mixtures thereof, in particular also racemic mixtures, and - as far as enantiomers possible - the respective biologically active enantiomers.
  • the compounds of the formulas (I) - (VI) can form salts, for example those in which the hydrogen of the -SO 2 -NH group is replaced by a cation suitable for agriculture.
  • These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else
  • Ammonium salts or salts with organic amines can take place by addition of an acid to basic groups, such as, for example, amino and alkylamino.
  • Suitable acids for this purpose are strong inorganic and organic acids, for example HCl, HBr, H 2 SO 4 or HNO 3 .
  • the herbicidal active compounds A) can inhibit the enzyme acetolactate synthase (ALS) and thus the protein synthesis in plants.
  • the application rate of the agrochemical active ingredients B) can vary within wide ranges, for example between 0.001 and 0.5 kg AS / ha.
  • the components A) and B) are preferably present in a synergistically effective amount.
  • the application rate ratio of components A): B) can vary within wide ranges, for example from 1:50 to 5: 1, preferably from 1:25 to 2.5: 1, more preferably from 1:15 to 2: 1.
  • the active compounds can generally be used as water-soluble wettable powder (WP) 1 water-dispersible granules (WDG), water-emulsifiable granules (WEG), suspoemulsion (SE), oil dispersion (OD), suspension concentrate (SC or FS), emulsifiable concentrate (EC), aqueous solutions (SL), emulsions (EW).
  • WP water-soluble wettable powder
  • WDG water-dispersible granules
  • WEG water-emulsifiable granules
  • SE suspoemulsion
  • OD oil dispersion
  • SC or FS suspension concentrate
  • EC emulsifiable concentrate
  • ratios A): B) are given above and denote the weight ratio of the two components A) and B) to each other.
  • a safener When using the active compounds A) in crops it may be appropriate, depending on the crop, to apply a safener from certain application rates in order to reduce or avoid any damage to the crop.
  • suitable safeners are those which, in combination with ALS inhibitors, e.g. Sulfonamide herbicides such as sulfonylureas, Safener Ober unfold.
  • Suitable safeners are e.g. from WO-A-96/14747 and the literature cited therein.
  • ⁇ A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, nitro or (C r C 4 ) haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (W A 1 ) to (W A 4 ),
  • rriA is 0 or 1
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated c-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, via the N atom with the Carbonyl group in (S 1) and is unsubstituted or substituted by radicals from the group (C 1 -C 4 alkyl, (C 1 -C 6 -alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 ,
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having in total 1 to 18 carbon atoms;
  • RA 4 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (CrC 8 ) AlCl y.
  • R A 9 is hydrogen, (C r C 8 ) alkyl, (d-Cs) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 6 ) hydroxyalkyl, (C 3 -d 2 ) cycloalkyl or TYi (C 1 -
  • R A 6, 7 RA, RA 8 are identical or different hydrogen, (d-C ⁇ JAlkyl, (CrC 8) halo- alkyl, (C 3 -C 2) cycloalkyl or substituted or unsubstituted phenyl;
  • dichlorophenylpyrazoline-3-carboxylic acid S1 a
  • compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid S1 a
  • compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid S1 a
  • compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid 1- (2,4-dichloro-phenyl) -5- (ethoxycarbonyl) -5-methyl-2- pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("mefenpyr-diethyl") and related compounds as described in WO-A-91/07874
  • dichlorophenylpyrazolecarboxylic acid derivatives S1 b
  • RB 1 is halogen, (CrC 4) alkyl, (CrC 4) alkoxy, nitro or (C r C 4) haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is ORB 3 , SR 6 3 or NR 8 3 RB 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, via the N atom is connected to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy or optionally substituted phenyl, preferably one
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) -alkoxy or substituted or unsubstituted phenyl;
  • T B is a (Ci or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4 ) alkyl radicals or by [(C 1 -C 3 ) alkoxy] carbonyl;
  • Rc 1 is (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 - C 7 ) cycloalkyl, preferably dichloromethyl;
  • Rc 2, rc 3 are identical or different hydrogen, (CrC 4) alkyl, (C 2 -C 4) -alkenyl AI,
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • X 0 is CH or N
  • R D 1 is CO-NRD 5 RD 6 or NHCO-R 0 7 ;
  • RD 2 is halogen, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylsulfonyl, (C 1 -C 4 ) alkoxycarbonyl or (C 1 -C 4 ) alkylcarbonyl;
  • RD 3 is hydrogen, (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R 0 4 is halo, nitro, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C r C 4 ) haloalkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (C r C 4 ) alkoxy , cyano, (C 1 -C 4) AI alkylthio, (Ci-C 4) alkylsulfinyl, (C r C 4) alkylsulfonyl, (C r C 4) alkoxycarbonyl or (C r C 4) alkylcarbonyl;
  • RD 5 is hydrogen, (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, (C 2 -C 6) -alkenyl AI, (C 2 -C 6) alkynyl, (C 5 -C 6) cycloalkenyl, Phenyl or 3- to 6-membered heterocyclyl containing
  • VD hetero atoms from the group nitrogen, oxygen and sulfur where the seven last-mentioned radicals are substituted by VD substituents selected from halogen, (CrC 6) alkoxy, (C 1 -C 6) HaIOaIkOXy, (C r C 2) alkylsulfinyl, (C 1 - C 2 ) alkylsulfonyl, (C 3 -C 6 ) cycloalkyl, (C r C 4 ) alkoxycarbonyl, (C 1 - C 4 ) alkylcarbonyl and phenyl and in the case of cyclic radicals also (C 1 -C 4 ) alkyl and (C - ⁇ -C 4 ) haloalkyl are substituted;
  • RD 6 is hydrogen, (C 1 -C 6 -alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, where the three latter radicals are represented by v D radicals from the group consisting of halogen, hydroxy, (C 1 -C 4 ) alkyl, (C 1 -C 4) -alkoxy and (CrC 4) alkylthio, or R 5 and RD 0 6 together with the the nitrogen atom carrying them a
  • R 0 7 is hydrogen, (C r C4) alkylamino, di ⁇ CrC ⁇ alkylamino, (C r C6) alkyl,
  • (C 3 -C 6 ) cycloalkyl where the 2 latter radicals by v D substituents selected from the group consisting of halogen, (C 1 -C 4 ) alkoxy, (C r C 6 ) haloalkoxy and (CrC 4 ) alkylthio and in the case of cyclic radicals also (Ci-C 4 ) alkyl and
  • n D is 0, 1 or 2
  • m D is 1 or 2
  • v D is 0, 1, 2 or 3;
  • (CrC 4 ) haloalkyl are substituted; R 0 4 halogen, (dC 4) alkyl, (C 1 -C 4) -alkoxy, CF 3; VD is 0, 1, 2 or 3;
  • Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744,
  • RD 8 and R D 9 independently of one another hydrogen, (CrC 8 ) Al kVl, (C 3 -C 8 ) cycloalkyl,
  • Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in US Pat WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • S5 Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid
  • S6 active compounds from the class of 1, 2-dihydroquinoxaline-2-ones (S6), e.g.
  • RE 1 , RE 2 are each independently halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (CrC 4 ) haloalkyl, (Ci-C 4 ) alkylamino, di (CrC 4 ) alkylamino, nitro;
  • a E is COORE 3 or COSR E 4
  • RE 3 , RE 4 are independently hydrogen, (C 1 -C 4 ) alkyl, (C 2 -
  • n E is O or 1
  • n ⁇ are independently O, 1 or 2
  • Phenyl optionally substituted phenoxy, RF 2 hydrogen or (C r C 4 ) alkyl RF 3 hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the
  • ⁇ F is an integer from 0 to 2
  • RF 2 is hydrogen or (C r C 4 ) alkyl
  • RF 3 is hydrogen, (C r C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably to to three identical or different radicals from the group consisting of halogen and alkoxy substituted, mean, or their salts.
  • S9 Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. 1, 2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS No. 95855-00-8), as described in WO-A-1999/000020.
  • S9 5-tetrazolylcarbonyl) -2-quinolones
  • YG, Z 6 independently of one another are O or S, n G is an integer from 0 to 4,
  • R 6 2 (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl,
  • RG 3 is hydrogen or (C r C 6 ) alkyl.
  • S11) oxyimino compound type compounds (S11) known as seed dressings such as those described in US Pat. B.
  • S12 active substances from the class of the isothiochromanones (S12), such as, for example, methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04- 6) (S12-1) and related compounds of WO-A-1998/13361. 513)
  • S12 isothiochromanones
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as
  • Pretilachlor is known in sown rice
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • the herbicide-azole combinations according to the invention are suitable for controlling harmful plants in plant crops, for example in economically important crops such as cereals (eg wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugarcane , Rapeseed, cotton and soy.
  • cereals eg wheat, barley, rye, oats, rice, corn, millet
  • sugar beet sugarcane
  • Rapeseed cotton and soy.
  • monocotyledonous crops such as cereals, e.g. Wheat, barley, rye, oats, rice, corn and millet.
  • herbicide-azole combinations which, in addition to the components A) and B), also contain one or more further agrochemical active substances of a different structure, e.g. from the group of herbicides,
  • herbicide / azole combinations containing the following compounds A) + B):
  • each of the abovementioned active compound combinations may also contain a safener, in particular a safener from the group mefenpyr-diethyl (S1-1), isoxadifen-ethyl (S1-11), cloquintocet-methyl (S2-1) and cyprosulfamide (S4-1 ).
  • a safener from the group mefenpyr-diethyl (S1-1), isoxadifen-ethyl (S1-11), cloquintocet-methyl (S2-1) and cyprosulfamide (S4-1 ).
  • the combinations according to the invention can be used together with other agrochemical active ingredients, for example from the group of safeners, fungicides, herbicides, insecticides and plant growth regulators, as well as additives customary in crop protection, such as adhesion, wetting, dispersing, emulsifying, preserving, antifreeze and solvents , Filling and
  • Carriers, defoamers, evaporation inhibitors or agents that affect the pH or viscosity are used.
  • the combinations according to the invention have an excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients.
  • the substances can be applied, for example, in pre-sowing, pre-emergence and / or post-emergence processes, for example jointly or separately. The application is preferably postemergence.
  • Called weed flora which can be controlled by the combinations according to the invention, without that by naming a restriction to certain species should be made.
  • the spectrum of activity extends to species such as e.g. Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. Galium aparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds.
  • species such as e.g. Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. Galium
  • the combinations according to the invention are applied to the surface of the earth before or during the germination phase, the emergence of the weed seedlings is inhibited or completely prevented, or the weeds grow to the ground Cotyledon stage, but then stop their growth and eventually die off after three to four weeks.
  • the combinations according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action.
  • the rainfastness of the active ingredients in the combinations according to the invention is generally favorable.
  • a particular advantage is the fact that the effective and used in the combinations dosages of drugs A) and B) can be set so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contamination is virtually avoided.
  • the combination of active substances according to the invention makes it possible to considerably reduce the required application rate of the active substances, which is described, for example, in US Pat. can lead to improved reproduction behavior.
  • the synergistic effects allow a reduction in the application rate, the control of a broader spectrum of weeds and weeds, a faster use of herbicidal activity, a longer lasting effect, better control of harmful plants with only one or a few applications and an extension of the possible period of application.
  • the said properties and advantages are useful in the practical weed control in order to keep agricultural crops free from undesired competing plants and thus to secure and / or increase the yields qualitatively and quantitatively.
  • the technical standard is significantly exceeded by these new combinations in terms of the properties described.
  • the combinations according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all.
  • the combinations according to the invention sometimes have excellent growth-regulatory properties in the crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as crop losses during storage can be reduced or completely prevented.
  • the combinations according to the invention can also be used for controlling harmful plants in genetically modified crops or those obtained by mutation selection.
  • crops are usually distinguished by particular advantageous properties, such as resistance to herbicidal agents or resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z.
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) which render plants resistant to certain pests (EP-A-0142924,
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • transgenic plants may in principle be plants of any plant species, ie both monocotyledonous and dicotyledonous plants.
  • the present invention further provides a method for controlling undesired plant growth, preferably in crops such as cereals (eg wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, more preferably in monocotyledonous crops such as cereals, eg Wheat, barley, rye, oats, rice, maize and millet, which comprises one or more active substances A) and one or more active substances B) together or separately on the plants, plant parts, plant seeds or the area on which the plants grow, e.g. the acreage, applied.
  • crops such as cereals (eg wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, more preferably in monocotyledonous crops such as cereals, eg Wheat, barley, rye, oats, rice, maize and millet, which comprises
  • the plant cultures may also be genetically modified or obtained by mutation selection and are preferably tolerant to acetolactate synthase (ALS) -I inhibitors.
  • ALS acetolactate synthase
  • the invention also provides the use of the combinations according to the invention for controlling harmful plants, preferably in plant crops.
  • the combinations of the invention may also be used non-selectively for controlling undesired plant growth, e.g. in plantation crops, on roadsides, squares, industrial plants or railway facilities.
  • the combinations according to the invention can be present both as mixed formulations of components A) and B), if appropriate with further agrochemical active ingredients and / or additives, which are then diluted with water in the customary manner be brought into use, or prepared as so-called tank mixes by co-diluting the separately formulated or partially separately formulated components with water.
  • the components A) and B) or combinations thereof can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined.
  • suitable formulation options are: wettable powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC or FS), oil-based dispersions (OD) or water-based, suspoemulsions (SE), dusts (DP), mordants, granules, eg for soil or litter application or water-dispersible granules (WDG) or water-emulsifiable granules (WEG), ULV formulations, microcapsules or waxes.
  • WP wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • EW emulsion
  • Injection powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, except for a diluent or inert substance, are also ionic or nonionic surfactants (wetting agents, dispersants), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate, or sodium oleoylmethyltaurine.
  • ionic or nonionic surfactants e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates,
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, XyIoI or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic or nonionic surfactants (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, XyIoI or higher-boiling aromatics or hydrocarbons.
  • emulsifiers which may be used are alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene
  • Dusts are obtained by grinding the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • SC Suspension concentrates
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can either be prepared by atomizing the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 2 to 95% by weight, of active compounds A) and / or B), the following concentrations being customary depending on the type of formulation:
  • the active ingredient concentration is about 10 to 95 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active substance concentration can be, for example, 5 to 80% by weight, be.
  • Dusty formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 0.2 to 25 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active substance formulations mentioned optionally contain the customary additives such as adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors or agents which control the pH or affect the viscosity.
  • customary additives such as adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors or agents which control the pH or affect the viscosity.
  • the herbicidal action of the herbicide-azole combinations according to the invention can be improved, for example, by surface-active substances, preferably by wetting agents from the series of fatty alcohol polyglycol ethers.
  • the fatty alcohol polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether section.
  • the fatty alcohol polyglycol ethers can be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates, are present that are, for example, as alkali metal salts (eg sodium and potassium salts) or ammonium salts, or as alkaline earth metal salts are used, such as C 2 / C 4 fatty alcohol diglykolethersulfat- sodium (Genapol ® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988).
  • Nonionic fatty alcohol polyglycol ethers are, for example, 2 - 20, preferably 3 - 15 ethylene oxide units containing (C 10 - Ci ⁇ ) -, preferably (Cio-Ci 4) -Fettalkohol- polyglycol ethers (for example isotridecyl alcohol polyglycol ether), for example from the Genapol ® X series as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Fa. Clariant).
  • Genapol ® X series as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Fa. Clariant).
  • Genapol ® X series as Genapol ® X-030, Genapol ® X-060, Genapol ®
  • vegetable oils is understood to mean oils from oil-supplying plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil or castor oil, in particular rapeseed oil, and their transesterification products, for example alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of Cio-C22- > preferably C12-C20 fatty acids.
  • the C O -C 22 -fatty acid esters are, for example, esters of unsaturated or saturated Cio-C 22 fatty acids, especially with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C-is-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Cio-C 22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the C 10 -C 22 fatty acids, as contained for example in oils from oil-yielding plant species, or CrC 2 o-alkyl-CioC 22- fatty acid esters, as can be obtained, for example, by transesterification of the aforementioned glycerol or glycol-Cio-C 22 - fatty acid esters with CrC 2 o-alcohols (eg, methanol, ethanol, propanol or butanol). The transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
  • CrC 2 o-alkyl-Cio-C 22 fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters.
  • glycol and glycerol-Cio-C 22 fatty acid esters are preferred, the uniform or mixed glycol esters and glycerol esters of C- ⁇ o-C 22 fatty acids, especially those
  • Straight-chain fatty acids eg erucic acid, lauric acid, palmitic acid and especially C 8 fatty acids, such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the vegetable oils can be used in the combinations according to the invention, for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten® (Victorian Chemical Company, Australia, below Hasten mentioned, main ingredient: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter ActirobB called Main Ingredient: (rapeseed oil), Renol ®: Rapsölmethylester), Rako-Binol ® (Bayer AG, Germany, termed Rako-Binol, main ingredient , hereinafter referred Stefes, Germany Renol, vegetable oil ingredient: Rapsölmethylester) be included: Rapsölmethylester) or Mero ® (Bayer CropScience, Germany, termed Mero, main constituent.
  • Hasten® Vanictorian Chemical Company, Australia, below Hasten mentioned, main ingredient: rapeseed oil ethyl ester
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or scattering granules, as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the active ingredients A) and B) can be applied together or separately to the plants, plant parts, plant seeds or the area on which the plants grow (for example the cultivated area), preferably to the green plants and plant parts and optionally additionally to the cultivated area.
  • One possibility of the application is the joint application of the active ingredients in the form of tank mixes, wherein the optimally formulated concentrated formulations of the individual active ingredients are mixed together in the tank with water and the resulting spray mixture is discharged.
  • a common formulation of the active ingredients of the herbicide-azole combination according to the invention has the advantage of easier applicability, because the amounts of the components are already set in the correct ratio to each other.
  • the additives in the formulation can be optimally matched to each other, while a tank mix of different formulations can give undesirable combinations of additives.
  • a dust is obtained by mixing 10 parts by weight of an active substance / active substance mixture and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by mixing 25 parts by weight of an active substance mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyltaurine sodium as network and
  • Dispersant mixed and ground in a pin mill.
  • a readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (7Triton ® X 207), 3 parts by weight
  • Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, e.g., about 255 to 277EC) and ground to a fineness of less than 5 microns in a ball mill.
  • Active substance / active substance mixture 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granule is obtained by mixing 75 parts by weight of an active substance / active substance mixture,
  • a water-dispersible granule is also obtained by adding 25 parts by weight of an active substance mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate , 1 part by weight of polyvinyl alcohol,
  • the seeds of typical harmful plants and of typical cereal plants were laid out, grown up and grown under greenhouse conditions.
  • the treatment with the agents according to the invention was carried out after emergence of harmful plants usually in the 2- to 4-leaf stage in different dosages with a water application rate of 300 l / ha.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une combinaison herbicide-azole présentant une certaine teneur en constituants (A) et (B), possédant des effets améliorés, (A) représentant un ou plusieurs ingrédients actifs herbicides du groupe des inhibiteurs de l'ALS et (B) représentant un ou plusieurs composés azole à action agrochimique, sélectionnés de préférence dans le groupe des triazoles, pyrazoles et triazolinethione.
PCT/EP2008/009681 2007-11-29 2008-11-15 Combinaison herbicide-azole WO2009068193A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US12/743,738 US8318637B2 (en) 2007-11-29 2008-11-15 Herbicide/azole combination
EP08855397A EP2224813A2 (fr) 2007-11-29 2008-11-15 Combinaison herbicide-azole

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07023140.2 2007-11-29
EP07023140A EP2064953A1 (fr) 2007-11-29 2007-11-29 Combinaison d'herbicide-azole

Publications (2)

Publication Number Publication Date
WO2009068193A2 true WO2009068193A2 (fr) 2009-06-04
WO2009068193A3 WO2009068193A3 (fr) 2010-04-08

Family

ID=39166547

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/009681 WO2009068193A2 (fr) 2007-11-29 2008-11-15 Combinaison herbicide-azole

Country Status (3)

Country Link
US (1) US8318637B2 (fr)
EP (2) EP2064953A1 (fr)
WO (1) WO2009068193A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102550585A (zh) * 2012-01-16 2012-07-11 河北博嘉农业有限公司 甲基二磺隆复配除草剂
WO2013127855A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide, herbicide et d'amélioration de la santé végétale dans des céréales

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013127820A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le colza
WO2013127843A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le tournesol

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0182740A2 (fr) * 1984-10-25 1986-05-28 Ciba-Geigy Ag Agents synergiques et procédé pour lutter sélectivement contre les mauvaises herbes, particulièrement dans les céréales
EP0612473A1 (fr) * 1993-02-26 1994-08-31 Monsanto Europe S.A./N.V. Combinaisons herbicides comprenant un dérivé de triazole et un herbicide de sulfonylurée
WO1996019110A2 (fr) * 1994-12-22 1996-06-27 Monsanto Company Compositions herbicides
WO1998035560A1 (fr) * 1997-02-12 1998-08-20 E.I. Du Pont De Nemours And Company Composition herbicide utilisee dans la recolte rizicole
WO1999065314A1 (fr) * 1998-06-16 1999-12-23 Basf Aktiengesellschaft Melanges herbicides a effet synergique
WO2002054867A1 (fr) * 2001-01-16 2002-07-18 Sumitomo Chemical Takeda Agro Company, Limited Composition contenant un derive de sulfonamide, destinee a l'agriculture et a l'horticulture
WO2003043422A1 (fr) * 2001-11-22 2003-05-30 Bayer Cropscience Gmbh Agents herbicides synergiques contenant des herbicides du groupes des benzopyrazols
WO2003051122A1 (fr) * 2001-12-19 2003-06-26 Basf Aktiengesellschaft Melange herbicide a base de 7-pyrazolylbenzoxazoles
WO2004004463A1 (fr) * 2002-07-08 2004-01-15 Basf Aktiengesellschaft Melanges herbicides a action synergique
WO2004008849A2 (fr) * 2002-07-22 2004-01-29 Basf Aktiengesellschaft Melanges herbicides a action synergique

Family Cites Families (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK163123C (da) 1978-05-30 1992-06-09 Du Pont Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse
US4443971A (en) 1979-10-16 1984-04-24 Cornell Research Foundation, Inc. Herbicide-tolerant plants
ZA806970B (en) 1979-11-30 1982-06-30 Du Pont Agricultural sulfonamides
DE3035554A1 (de) 1980-09-20 1982-05-06 Hoechst Ag, 6000 Frankfurt Herbizide mittel
MA19709A1 (fr) 1982-02-17 1983-10-01 Ciba Geigy Ag Application de derives de quinoleine a la protection des plantes cultivees .
EP0094349B1 (fr) 1982-05-07 1994-04-06 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
WO1984002919A1 (fr) 1983-01-17 1984-08-02 Monsanto Co Plasmides de transformation de cellules vegetales
BR8404834A (pt) 1983-09-26 1985-08-13 Agrigenetics Res Ass Metodo para modificar geneticamente uma celula vegetal
JPS6087254A (ja) 1983-10-19 1985-05-16 Japan Carlit Co Ltd:The 新規尿素化合物及びそれを含有する除草剤
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
DE3525205A1 (de) 1984-09-11 1986-03-20 Hoechst Ag, 6230 Frankfurt Pflanzenschuetzende mittel auf basis von 1,2,4-triazolderivaten sowie neue derivate des 1,2,4-triazols
BR8600161A (pt) 1985-01-18 1986-09-23 Plant Genetic Systems Nv Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio
DE3680212D1 (de) 1985-02-14 1991-08-22 Ciba Geigy Ag Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen.
US5010195A (en) 1988-05-25 1991-04-23 The Dow Chemical Company Herbicidal alkoxy-1,2,4-triazolo(1,5-c)primidine-2-sulfonamides
EP0221044B1 (fr) 1985-10-25 1992-09-02 Monsanto Company Vecteurs de plantes
AU587539B2 (en) 1986-06-14 1989-08-17 Ihara Chemical Industry Co. Ltd. Picolinic acid derivatives and herbicidal compositions
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
IL83348A (en) 1986-08-26 1995-12-08 Du Pont Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
DE3633840A1 (de) 1986-10-04 1988-04-14 Hoechst Ag Phenylpyrazolcarbonsaeurederivate, ihre herstellung und verwendung als pflanzenwachstumsregulatoren und safener
US5078780A (en) 1986-10-22 1992-01-07 Ciba-Geigy Corporation 1,5-diphenylpyrazole-3-carboxylic acid derivatives for the protection of cultivated plants
DE3853622T2 (de) 1987-12-22 1996-01-11 Ihara Chemical Ind Co Pyrimidin-Derivate, Verfahren zu deren Herstellung und herbizide Methode und Zusammenstellungen.
DE3808896A1 (de) 1988-03-17 1989-09-28 Hoechst Ag Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten
DE3809159A1 (de) 1988-03-18 1989-09-28 Hoechst Ag Fluessige herbizide mittel
US5057144A (en) 1988-05-09 1991-10-15 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
DE3817192A1 (de) 1988-05-20 1989-11-30 Hoechst Ag 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols
EP0365484B1 (fr) 1988-10-20 1993-01-07 Ciba-Geigy Ag Sulfamoylphénylurées
US5162602A (en) 1988-11-10 1992-11-10 Regents Of The University Of Minnesota Corn plants tolerant to sethoxydim and haloxyfop herbicides
US4988812A (en) 1989-11-06 1991-01-29 Dow Elanco Aqueous process for the preparation of 5-methyl-n-(aryl)-1,2,4-triazolo(1,5-A)pyrimidine-2-sulfonamides
DE3939010A1 (de) 1989-11-25 1991-05-29 Hoechst Ag Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschuetzende mittel
DE3939503A1 (de) 1989-11-30 1991-06-06 Hoechst Ag Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden
CA2077896C (fr) 1990-03-16 2008-02-19 Gregory A. Thompson Desaturases vegetales - compositions et utilisations
ATE212670T1 (de) 1990-06-18 2002-02-15 Monsanto Technology Llc Erhöhter stärkegehalt in pflanzen
JPH04103574A (ja) 1990-08-22 1992-04-06 Kumiai Chem Ind Co Ltd ピリミジン誘導体及び除草剤
DE4029304A1 (de) 1990-09-15 1992-03-19 Hoechst Ag Synergistische herbizide mittel
EP0492366B1 (fr) 1990-12-21 1997-03-26 Hoechst Schering AgrEvo GmbH Nouveaux dérivés de chloro-5-quinoline-8-acide oxyalkanecarboniques, procédé pour leur préparation et leur utilisation comme antidote d'herbicides
SE467358B (sv) 1990-12-21 1992-07-06 Amylogene Hb Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp
WO1992011761A1 (fr) 1990-12-31 1992-07-23 Monsanto Company Reduction des interactions pesticides dans les recoltes
DE4104782B4 (de) 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide
US5534486A (en) 1991-04-04 1996-07-09 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
TW259690B (fr) 1992-08-01 1995-10-11 Hoechst Ag
DE4331448A1 (de) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Substituierte Isoxazoline, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener
DE4440354A1 (de) 1994-11-11 1996-05-15 Hoechst Schering Agrevo Gmbh Kombinationen aus Phenylsulfonylharnstoff-Herbiziden und Safenern
DE19621522A1 (de) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung
WO1998013361A1 (fr) 1996-09-26 1998-04-02 Novartis Ag Composition herbicide
DE19652961A1 (de) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Neue 2-Fluoracrylsäurederivate, neue Mischungen aus Herbiziden und Antidots und deren Verwendung
US6071856A (en) 1997-03-04 2000-06-06 Zeneca Limited Herbicidal compositions for acetochlor in rice
DE19727410A1 (de) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-Tetrazolylcarbonyl)-2-chinolone und diese enthaltende nutzpflanzenschützende Mittel
DE19742951A1 (de) 1997-09-29 1999-04-15 Hoechst Schering Agrevo Gmbh Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung
AR031027A1 (es) 2000-10-23 2003-09-03 Syngenta Participations Ag Composiciones agroquimicas
WO2004008861A1 (fr) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Melanges herbicides agissant de façon synergique
KR20060002857A (ko) 2003-03-26 2006-01-09 바이엘 크롭사이언스 게엠베하 독성 완화제로서의 방향족 하이드록시 화합물의 용도
DE10335726A1 (de) 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Verwendung von Hydroxyaromaten als Safener
DE10335725A1 (de) 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Safener auf Basis aromatisch-aliphatischer Carbonsäuredarivate
DE102004023332A1 (de) 2004-05-12 2006-01-19 Bayer Cropscience Gmbh Chinoxalin-2-on-derivate, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung und deren Verwendung
DE102005031787A1 (de) * 2005-07-07 2007-01-18 Bayer Cropscience Gmbh Kulturpflanzenverträgliche herbizide Mittel enthaltend Herbizide Safener
JPWO2007023719A1 (ja) 2005-08-22 2009-02-26 クミアイ化学工業株式会社 薬害軽減剤及び薬害が軽減された除草剤組成物
WO2007023764A1 (fr) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0182740A2 (fr) * 1984-10-25 1986-05-28 Ciba-Geigy Ag Agents synergiques et procédé pour lutter sélectivement contre les mauvaises herbes, particulièrement dans les céréales
EP0612473A1 (fr) * 1993-02-26 1994-08-31 Monsanto Europe S.A./N.V. Combinaisons herbicides comprenant un dérivé de triazole et un herbicide de sulfonylurée
WO1996019110A2 (fr) * 1994-12-22 1996-06-27 Monsanto Company Compositions herbicides
WO1998035560A1 (fr) * 1997-02-12 1998-08-20 E.I. Du Pont De Nemours And Company Composition herbicide utilisee dans la recolte rizicole
WO1999065314A1 (fr) * 1998-06-16 1999-12-23 Basf Aktiengesellschaft Melanges herbicides a effet synergique
WO2002054867A1 (fr) * 2001-01-16 2002-07-18 Sumitomo Chemical Takeda Agro Company, Limited Composition contenant un derive de sulfonamide, destinee a l'agriculture et a l'horticulture
WO2003043422A1 (fr) * 2001-11-22 2003-05-30 Bayer Cropscience Gmbh Agents herbicides synergiques contenant des herbicides du groupes des benzopyrazols
WO2003051122A1 (fr) * 2001-12-19 2003-06-26 Basf Aktiengesellschaft Melange herbicide a base de 7-pyrazolylbenzoxazoles
WO2004004463A1 (fr) * 2002-07-08 2004-01-15 Basf Aktiengesellschaft Melanges herbicides a action synergique
WO2004008849A2 (fr) * 2002-07-22 2004-01-29 Basf Aktiengesellschaft Melanges herbicides a action synergique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2224813A2 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102550585A (zh) * 2012-01-16 2012-07-11 河北博嘉农业有限公司 甲基二磺隆复配除草剂
WO2013127855A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide, herbicide et d'amélioration de la santé végétale dans des céréales

Also Published As

Publication number Publication date
EP2224813A2 (fr) 2010-09-08
US8318637B2 (en) 2012-11-27
WO2009068193A3 (fr) 2010-04-08
EP2064953A1 (fr) 2009-06-03
US20100255995A1 (en) 2010-10-07

Similar Documents

Publication Publication Date Title
EP1411767B1 (fr) Combinaisons herbicides contenant des sulfonylurees specifiques
EP1104232B2 (fr) Herbicides
EP1482801B1 (fr) Combinaisons herbicides avec des sulfonylurees particulieres
EP1418812B1 (fr) Associations herbicides contenant des urees de sulfonyle speciales
EP3493677B1 (fr) Concentrés de suspension en capsule à base de 2-(2,4-dichlorobenzyl)-4,4-diméthyl-isoxazolidin-3-one
WO2006072359A1 (fr) Association de substances actives herbicides synergiques
EP2091332A2 (fr) Combinations herbicides comprenant de l&#39;amidosulfuron et d&#39;un herbicide pyridinique
WO2009068193A2 (fr) Combinaison herbicide-azole
WO2005011378A1 (fr) Concentre en suspension huileuse contenant du diflufenican
EP3639664A1 (fr) Combinaisons d&#39;herbicides
US10863742B2 (en) Herbicide combinations
JP2011500743A (ja) ２−ヨード−ｎ−［（４−メトキシ−６−メチル−１，３，５−トリアジン−２−イル）カルバモイル］ベンゼンスルホンアミドおよび／またはその塩および１，３−ジケト化合物群からの除草活性化合物を含有する除草剤組み合わせ
JP2011500746A (ja) ２−ヨード−ｎ−［（４−メトキシ−６−メチル−１，３，５−トリアジン−２−イル）カルバモイル］ベンゼンスルホンアミドおよび／またはその塩およびフェニルエーテル群からの除草活性化合物を含有する除草剤組み合わせ
EP4362680A1 (fr) Compositions herbicides contenant de la cinméthyline et de l&#39;éthofumesate
CA3221977A1 (fr) Compositions comprenant de l&#39;ethofumesate et un phytoprotecteur
EP3639665A1 (fr) Combinaisons d&#39;herbicides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08855397

Country of ref document: EP

Kind code of ref document: A2

REEP Request for entry into the european phase

Ref document number: 2008855397

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2008855397

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 12743738

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE